Its a bit off track from your post, but i've been wondering about this gated community... would a place like that be considered private property meant only for those paying to live there? i'm wondering if the kid was trespassing by regularly cutting through there.

This nation will probably never call him a hero, but the other residents of that place were quite stalwart in his defense as i recall, i'm guessing they'd had enough of the break ins and were on edge about it.

I believe Florida Gated Communities are considered private which would include any walkways, street and sidewalks.
So permission would be needed to get in. It may be done differently in different areas.